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Additionsreaktionen von 2-Amino-1-azetinen mit Cyclopropenonen; Bildung von Azepinderivaten durch Ringerweiterung


Stierli, Friedrich; Prewo, Roland; Bieri, Jost H; Heimgartner, Heinz (1983). Additionsreaktionen von 2-Amino-1-azetinen mit Cyclopropenonen; Bildung von Azepinderivaten durch Ringerweiterung. Helvetica Chimica Acta, 66:1366-1375.

Abstract

Addition Reactions of 2-Amino-1-azetines with Cyclopropenones; Formation of Azepine Derivatives by Ring Expansion Reactions. The reaction of 2-amino-1-azetines of type 6 with 2,3-diphenylcyclopropenone (1a) in acetonitrile leads to azeto[1,2-a]pyrroles (cf: 7 and 9, Schemes 3 and 4) in good yield. It is remarkable that in the reaction of 6a with 1a only endo-7 is formed. With silicagel in ether endo-7 isomerizes to the thermodynamically more stable exo-7 (Schemes 3 and 6). The crystal structure of the latter compound has been established by X-ray crystallography. The reaction of 6a and 2-isopropyl-3-phenyl- cyclopropenone (1b) yields only one product, which isomerizes with silicagel in ether to exo-10 (Scheme 4). The structure of exo-10 has been determined by NMR- spectroscopy. It seems reasonable that this structure results from a nucleophilic attack of the four-membered amidine to the phenyl-substituted C-atom of 1b.

Abstract

Addition Reactions of 2-Amino-1-azetines with Cyclopropenones; Formation of Azepine Derivatives by Ring Expansion Reactions. The reaction of 2-amino-1-azetines of type 6 with 2,3-diphenylcyclopropenone (1a) in acetonitrile leads to azeto[1,2-a]pyrroles (cf: 7 and 9, Schemes 3 and 4) in good yield. It is remarkable that in the reaction of 6a with 1a only endo-7 is formed. With silicagel in ether endo-7 isomerizes to the thermodynamically more stable exo-7 (Schemes 3 and 6). The crystal structure of the latter compound has been established by X-ray crystallography. The reaction of 6a and 2-isopropyl-3-phenyl- cyclopropenone (1b) yields only one product, which isomerizes with silicagel in ether to exo-10 (Scheme 4). The structure of exo-10 has been determined by NMR- spectroscopy. It seems reasonable that this structure results from a nucleophilic attack of the four-membered amidine to the phenyl-substituted C-atom of 1b.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1983
Deposited On:09 Jul 2014 12:44
Last Modified:05 Apr 2016 17:57
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:F. Hoffmann-La Roche & Co. AG, Basel, Prof. Hans-E. Schmid-Stiftung, Stipendienfonds der Basler Chemischen Industrie

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